I want to try milking this weekend

Discussion in 'Chastity and orgasm denial' started by MistressAshley, Feb 12, 2016.

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  1. MistressAshley
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    This weekend I was planning on milking my sissy. I have attempted to milk him once before and it was unsuccessful. He felt pleasure as he came, he does not deserve pleasure therefore I want to find a way to properly milk him so that the cum drips out of him and he feels nothing.
     
  2. Luscious-Liza
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    Hi Ashley
    I find a nice large dildo dose the job nicely, ,
    let it hit her G spot and wiggle it against it slowly
    make her grind on it she should start dripping after a while
    Make sure she empties her bladder I find that to help my bitch:)
     
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  3. Living Curious
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    Living Curious Long-term lockee

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    Make him watch American political news coverage while you're doing it. That should do the trick.
     
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  4. ChasteHubby2015
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    ChasteHubby2015 Male Feminist

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    Good of you to want to empty her without any pleasure. Have her pee put everything first and no.2 also, if any. Then just be patient and very gentle, I think it just takes time. I wouldn't imagine she'd feel anything if she's locked up tightly and you do it gently. Good luck.
     
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  5. Burger_01
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    Burger_01 Chastity Geek

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    I guess pleasure is a relative concept. Do I feel pleasure when my prostate is massaged? Absolutely! Is it the same pleasure I'd get from full orgasm? No.

    I guess the best you could do to strip away any pleasure he feels during milking is to make it as mundane and routine as possible. Schedule a time and stick to it, make the setup, and the process identical each time, and make it boring. Show him how bored you are with the process.. You know, about the same level of excitement you'd show while cleaning the bathroom. You could also try numbing creams on the cock and balls, and maybe the ass (not sure how that would go. Could sting a lot)

    This makes the process very distinct from a sexy romantic time (if you have those), and just a boring part of life, which takes all the fun out of it.
     
  6. Lucy
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  7. MistressAshley
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    All the advice helped a lot :)
    The milking was a big success this time, it actually worked! The milking did take awhile like you warned about and he needed a few breaks during the milking but in the end I milked her into a little doggy bowl and made her drink it like a little good girl. I was very pleased with the results :)
     
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  8. ChasteHubby2015
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    ChasteHubby2015 Male Feminist

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    Congratulations @MistressAshley :) I'm very happy for your success! I guess this throws out any health related excuses about her length of time in chastity. You can now keep her locked up in chastity indefinitely with weekly milkings.
     
  9. tommy619
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    tommy619 Long term member

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    Ive never been milked here. Sounds like its not as easy as it sounds though.
     
  10. Dufty
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    Dufty Long term member

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    Very well done! The doggy bowl is an excellent idea. Look forward to your next update.
     
  11. Subnumb
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    @MistressAshley
    What worked?

    Our experience.
    Wifey used her strapon (Tantus O2 Cush) over the weekend. I could only take the head. After she was done, there was a puddle under me. (She had me doggy style.) I didn't feel a thing as far as the oenis is concerned. She can't wait to try again. This weekend the objective wasn't to milk me. It happened unintentionally. We think, it was due to the size of the dildo- that is ended up massaging the right places for the milking to occur.
    For what it's worth, having my prostrate massaged is just about the worst feeling I can imagine.
     
  12. sandman9355
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    sandman9355 Junior Member

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    Could you maybe elaborate on that "worst feeling I can imagine" aspect? I'm not trying to say you have to find the experience pleasurable or at least neutral; my question is more like what exactly you find so unpleasant during the act.

    Is it the physical sensations? Does it make you hornier but still denied? Is it the psychological impact? Something else? More/all of the above?

    You see, given how many chastity enthusiasts want to be milked even when they *know* it will keep them frustrated and denied, seeing it described as "the worst feeling I can imagine" makes one wonder why you feel that way. Especially when a different kind of prostate massage can lead to an anal orgasm for some men.
     
  13. Subnumb
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    Supposed different strokes for different strokes.
    Sensation from prostrate stimulation is difficult to describe. I guess I find the added feeling of pressure aweful, along with the "zinging" feeling.
    All of that being said, I enjoy being pegged quite a bit. I just find prostrate stimulation aweful.
    I know my answer is short on inforfamtion; it is after all an explanation of liking a thing, which is an entirely subjective matter.
     
  14. harddenial
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    After more than a month of chastity I found my weekend milking a real relief. The Njoy pure wand extracted the equivalent of several orgasms worth of fluid. I don't find the massaging of the prostate to be particularly enjoyable because it is intensely frustrating because you can feel part of the orgasm process happening, but it doesn't go to completion. For an hour or two afterwards I literally felt a bit "weak-legged" with a dull but not painful ache in my groin which I realised reflected the lack of completion.
     
  15. salonslave
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    salonslave I play for a living and work for fun.

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    Many years ago I had a case pf prostatitis. I couldn't pee yet I needed to pee all the time. I went to the urologist before they opened in the morning. I could hardly walk for the pain. Doc said to bend over and he used his finger to press right where it hurt the most, my prostate gland. Ahhhhhh! After he had expressed it and looked at a sample through the microscope he gave me an antibiotic scrop and orders to return in 9 days. He pressed it again and this time it felt weird but didn't hurt.
    I am thinkingyou might have a bug since it hurts so much to be pressed. I would ho see the doc.
    Ss
     
  16. Junebug15
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    Junebug15 Long term member

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    Some have all the luck!
     
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